Driving Jobs in Chesapeake, VA — Open Positions

As of May 2026, there are 240+ open driving positions in Chesapeake, VA. Current pay ranges from $460 to $10,000 per year. Top hiring areas include Delivery Driver, General and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

FreshDrop Logistics

Start ASAP:Driver Opportunity(Chesapeake)

Chesapeake, VA

$3,000 - $5,500

Uber

Chesapeake Contractor Ubereats Delivery Driver | Hiring

Chesapeake, VA

$2,500 - $4,500

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Chesapeake, VA

$2,800 - $4,800

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Chesapeake, VA

$2,875 - $5,175

Heavy Freight Logistics

Chesapeake,VA:Independent Contractor Driver-Cargo Van / Box Truck

Chesapeake, VA

$5,000 - $8,500

CareDrop Couriers

Pharmacy Delivery Courier (Last-Mile Healthcare)

Chesapeake, VA

$3,000 - $4,500

Uber

Flexible Ubereats Large Order Delivery Driver(Chesapeake)

Chesapeake, VA

$3,675 - $6,300

Heavy Freight Logistics

Chesapeake Independent Contractor Driver-Cargo Van / Box Truck

Chesapeake, VA

$5,250 - $8,925

Grubhub

Campus Area Grubhub Driver

Chesapeake, VA

$2,989 - $5,520

Regional Auto Dealership Group

Regional Auto Dealership Group is hiring a OEM Dealership Auto Parts

Chesapeake, VA

$3,000 - $4,500

Sysco Corporation

Flexible Sysco Local CDL-A Delivery Truck Driver(Chesapeake)

Chesapeake, VA

$6,000 - $9,000

Grubhub

Flexible Part-Time Bicycle & Scooter Courier in Chesapeake | Part

Chesapeake, VA

$2,500 - $4,500

Driving Jobs in Chesapeake — FAQ

How many driving jobs are available in Chesapeake, VA right now?
There are currently 240+ open driving positions in Chesapeake, VA. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Chesapeake?
Driving job pay in Chesapeake varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Chesapeake?
Yes. Many delivery driver, courier, and DSP positions in Chesapeake require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Chesapeake?
Driving jobs in Chesapeake offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Chesapeake?
Benefits vary by employer, but many driving positions in Chesapeake offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Chesapeake?
Your take-home pay as a driver in Chesapeake depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Chesapeake?
Yes, many driving positions in Chesapeake are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 240+ listings above and apply directly.

Last updated: May 08, 2026